Chemistry:Pelanserin

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Pelanserin (developmental code name TR-2515) is a serotonin 5-HT2 and α1-adrenergic receptor antagonist which was under development for the treatment of hypertension but was never marketed.[1][2] Its development was discontinued in 2001.[1]

Pharmacology

Pharmacokinetics

The pharmacokinetics of pelanserin have been studied.[3] It has a relatively short elimination half-life.[4][3] The drug's time to peak levels was less than 1 hour and its half-life was 3.8 hours in a single subject in an analytical study.[5]

Chemistry

Synthesis

Synthesis of pelanserin

Pelanserin (3) can be synthesized by a reaction between isatoic anhydride (1) and 1-(3-aminopropyl)-4-phenylpiperazine (2) in the presence of phosgene.[6][7][8][9][10][11][12][13]

See also

References

  1. ↑ 1.0 1.1 "Pelanserin". 30 August 2002. https://adisinsight.springer.com/drugs/800001361. 
  2. ↑ "The 5-HT2 receptor antagonist, pelanserin, inhibits alpha 1-adrenoceptor-mediated vasoconstriction in vitro". European Journal of Pharmacology 277 (2–3): 181–185. April 1995. doi:10.1016/0014-2999(95)00074-u. PMID 7493607. 
  3. ↑ 3.0 3.1 "Pharmacokinetics of pelanserin in healthy volunteers". Proceedings of the Western Pharmacology Society 35: 113–116. 1992. PMID 1502209. 
  4. ↑ "Influence of admixed citric acid on the release profile of pelanserin hydrochloride from HPMC matrix tablets". International Journal of Pharmaceutics 201 (2): 165–173. May 2000. doi:10.1016/s0378-5173(00)00406-3. PMID 10878323. "Pelanserin is a weakly basic experimental drug with a short half-life and a prolonged release formulation was developed using hydroxypropyl methylcellulose (HPMC) and citric acid to set up a system bringing about gradual release of this drug.". 
  5. ↑ Cite error: Invalid <ref> tag; no text was provided for refs named Flores-Murrieta_1988
  6. ↑ "New sedative and hypotensive 3-substituted 2,4(1H,3H)-quinazolinediones". Journal of Medicinal Chemistry 8 (6): 807–815. November 1965. doi:10.1021/jm00330a017. PMID 5885076. 
  7. ↑ "Derivatives of 1,3-disubstituted 2,4(1H,3H)-quinazolinediones as possible peripheral vasodilators or antihypertensive agents". Journal of Medicinal Chemistry 22 (12): 1548–1550. December 1979. doi:10.1021/jm00198a024. PMID 231656. 
  8. ↑ "Synthesis of Deuterium-Labeled Antihypertensive 3-(4-Phenyl-1′-Piperazinyl)-Propyl-2,4-Quinazolinedione". Synthetic Communications 30 (15): 2707–2711. 2000. doi:10.1080/00397910008086895. 
  9. ↑ "Concise Synthesis of Pelanserine, Goshuyuamide II, and Wuchuyuamide II with Quinazolinedione Nuclei". Bulletin of the Korean Chemical Society 32 (9): 3480–3482. 2011. doi:10.5012/bkcs.2011.32.9.3480. 
  10. ↑ "Synthesis of Quinazolinedione Using Triphosgene". Synthetic Communications 21 (2): 285–292. 1991. doi:10.1080/00397919108020823. 
  11. ↑ "Verfahren zur Herstellung von neuen Chinazolindionderivaten und ihrer Säureadditionssalze bzw. ihrer entsprechenden Piperaziniumverbindungen [Process for the preparation of new quinazolinedione derivatives and their acid addition salts or their corresponding piperazinium compounds]" AT patent 269143B, published 1969-03-10, assigned to Miles Laboratories, Inc.
  12. ↑ Shin H, "Quinazolinedione derivatives", US patent 3274194, issued 20 September 1966
  13. ↑ Vidrio H, "Method of producing vasodilation using certain 3-substituted-quinazoline derivatives", US patent 3919425, issued 11 November 1975



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